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Love Your Information! Help with itinerary in Sept/Oct

I am trying to plan a trip to Florence and Rome in September or October. I have several questions for you, if you don't mind....I will try to be specific. I am Senior and am taking my granddaughter (over 18) for a "surprise" trip. We are thinking of either flying into Rome or into Pisa/Florence and leaving Rome or Florence. Is one way more preferable than the other? I want to take the train to either location. If we come in October, would it be cold? Just thinking the later we go the less crowded?

1. We want to see Pisa, Montepulciano, Siena and Chianti. I thought it would be fun for us to rent a Vespa for one day and go to Chianti (winetasting) since it is the closest place, then rent a car for the rest of time there. I was thinking three nights there. I also thought it would be fun to take the train to Venice for a day - just so she can see the gondolas and a few sights. Where would be our best place for a home base - Florence?

2. Would also want to take a cooking class - like making pasta I think would be fun for her. Any suggestions for that?